Sodium → HCID 178513089, compound

HRID 733222Notes

Reaction equation

HRID 733222 reaction equation
[Na].[Cl-].[NH2:3][C:4]([NH2:6])=[NH2+:5].[CH2:7]([N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]1[CH2:24][C:25](OCC)=[O:26])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(O)C>[CH2:7]([N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]1[CH2:24][C:25]([NH:5][C:4]([NH2:6])=[NH:3])=[O:26])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 5360545Sodium2×HCID 5460839Carbamimidoylazanium ChlorideHCID 12094383HCID 12094383, compound

Product 1

HCID 178513089HCID 178513089, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
20 °C

Procedure

0.22 g of sodium is added to 20 cm3 of absolute ethanol under an inert atmosphere. After the sodium has totally disappeared, 0.94 g of guanidinium chloride is added. The reaction mixture is stirred under an inert atmosphere at a temperature in the region of 20° C. for 1 hour, followed by addition of a solution of 2 g of ethyl (2-benzyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate in 5 cm3 of absolute ethanol. The reaction mixture is stirred at a temperature in the region of 20° C. for 18 hours and is then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue is taken up in a mixture of 10 cm3 of water and 30 cm3 of diethyl ether and is then stirred at a temperature in the region of 0° C. for 15 minutes. The precipitate obtained is filtered off, washed with twice 10 cm3 of ice-cold water and then dried in a desiccator under reduced pressure (2 kPa) at a temperature in the region of 20° C. 1.2 g of N-[(2-benzyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine are thus obtained in the form of a white powder melting at 222-225° C. Infrared spectrum (KBr) 3488; 3410; 3344; 1662; 1621; 1521; 1382 and 704 cm−1.

Workup

  1. stirringThe reaction mixture is stirred at a temperature in the region of 20° C. for 18 hours
  2. concentrationis then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  3. additionThe residue is taken up in a mixture of 10 cm3 of water and 30 cm3 of diethyl ether
  4. stirringis then stirred at a temperature in the region of 0° C. for 15 minutes
  5. customThe precipitate obtained
  6. filtrationis filtered off
  7. washwashed with twice 10 cm3 of ice-cold water
  8. customdried in a desiccator under reduced pressure (2 kPa) at a temperature in the region of 20° C

Sources & evidence

ORD record
ord-d5a38245686a40dab272e980b431bc05
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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